Sodium cyanoborohydride → 5-[3-(Indan-2-yloxy)-4-Methoxyphenyl]-1,2,3,4-Tetrahydro-2-Pyrimidinone
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]([C:19]2[CH:20]=[N:21][C:22](=[O:25])[NH:23][CH:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[BH3-]C#N.[Na+]>C(O)(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]([C:19]2[CH2:24][NH:23][C:22](=[O:25])[NH:21][CH:20]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]Participants
4
Procedure
5-[3-(Indan-2-yloxy)-4-methoxyphenyl]-1,2-dihydro-2-pyrimidinone (740 mg, 2.2 mmol) is dissolved in 10 ml. acetic acid cooled in an ice bath and treated with NaCNBH3 (140 mg, 2.2 mmol). The reaction is stirred for hours and is worked up by dilution with water and extraction with ethyl acetate. The collected organics are washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 640 mg (87.4%) of the title product as a white crystalline solid.